They dictate your process and are likely online.

The tree removal quotes were extremely high, with one company quoting $19,000, citing that I would go through the insurance company.

Financing available as high as 90% loan to value on real aggressive terms. 

The 'what you get' for the money factor is highly applicable from Brookings to Astoria and licensable STR coastal vacation rentals are still regularly attainable at workable terms, Luxury and oceanfront and lakefront properties tend to perform above the 10% of valuation in gross annual income for prime coastal STR's and as an example I've seen a $2.1 Million Oceanfront home produce $300k in gross annual income.

Do you recommend investing there now, and why or why not?

  $2,500 for an updated place / fresh paint & finishes.The house is not updated, and could use paint, etc. so I am reluctant to adjust too high too quickly. 

If you need investor-friendly agent recommendations in Wisconsin or Indiana, shoot me a DM.

My question would be is it recommended  to remodel some of the house?

I have some points on Supplement B, but not nearly enough to qualify as all my effort was on closing high-value deals that fall under A.

If you're looking to invest long term and build a portfolio, I'd recommend going with a 2-4 unit and take advantage of the VA financing.